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Publikācija: 1-Amino-1-hydroxymethylcyclobutane Derivatives via Intramolecular Amination of Nonclassical Cyclopropylmethyl Cation

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language 1-Amino-1-hydroxymethylcyclobutane Derivatives via Intramolecular Amination of Nonclassical Cyclopropylmethyl Cation
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Marija Skvorcova
Liene Grigorjeva
Aigars Jirgensons
Keywords amino alcohol, carbenium ion, cyclobutane, 5-oxa-7-azaspiro[2.5]oct-6-ene, 5-oxa-7-azaspiro[3.4]oct-5-ene, 1,3-oxazine, oxazoline, trichloroacetimidate, Lewis acid.
Abstract Bis(trichloroacetimidoyloxymethyl)cyclopropa nes provide intramolecular amination products of intermed iate cyclobutyl or cyclopr opyl-methyl carbenium ion when exposed to Lewis acid catalyst or thermal ionization. The ratio of the two amination products of cyclobutyl carbenium ion depends primarily on the substituent at the alkoxymet hyl group of the substrate and can be altered by the solvent used and the ionization conditions. An oxazoline deri vative forms as the major amination produc t in the case of unsubstituted bis(trichl o-roacetimidoyloxymethyl)cyclopropane or if the substrate contains isopropyl or alkoxymethyl substituents. The amination of cyclobutyl carbenium ion formed in situ proceeds with high diastereoselectivity leading to exclusive formation of trans- cyclobutane derivatives. The latter can be transformed to N-Boc-protected cyclobutane-based amino alcohols in high yields.
DOI: 10.1007/s10593-017-2162-1
Hyperlink: http://hgs.osi.lv/index.php/hgs/article/view/3996 
Reference Skvorcova, M., Grigorjeva, L., Jirgensons, A. 1-Amino-1-hydroxymethylcyclobutane Derivatives via Intramolecular Amination of Nonclassical Cyclopropylmethyl Cation. Chemistry of Heterocyclic Compounds, 2017, Vol.53, No.9, pp.989-996. ISSN 0009-3122. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-017-2162-1
Additional information Citation count:
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ID 26245